Water → Methyl 3-benzyloxy-3-phenyl-2-(4,6-dimethoxy-2-pyrimidinyl)oxybutyrate

HRID 1941106Notes

Reaction equation

HRID 1941106 reaction equation
[CH2:1]([O:8][C:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:16])[CH:10]([OH:15])[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:25][O:26][C:27]1[CH:32]=[C:31]([O:33][CH3:34])[N:30]=[C:29](S(C)(=O)=O)[N:28]=1.O>CN(C)C=O.C(O)(=O)C>[CH2:1]([O:8][C:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:16])[CH:10]([O:15][C:29]1[N:30]=[C:31]([O:33][CH3:34])[CH:32]=[C:27]([O:26][CH3:25])[N:28]=1)[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 15292268Methyl 3-benzyloxy-3-phenyl-2-hydroxybutyrate2×

Product 1

HCID 15292273Methyl 3-benzyloxy-3-phenyl-2-(4,6-dimethoxy-2-pyrimidinyl)oxybutyrate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

3 g (10 mmol) of methyl 3-benzyloxy-3-phenyl-2-hydroxybutyrate (compound 1.1) are dissolved in 40 ml of dimethylformamide, and 0.3 g (12 mmol) of sodium hydride are added. Stirring is carried out for 1 hour, after which 2.2 g (10 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine are added. After stirring has been carried out for 24 hours at room temperature, hydrolysis is effected carefully with 10 ml of water, the pH is brought to 5 with acetic acid and the solvent is distilled off under greatly reduced pressure. The residue is taken up in 100 ml of ethyl acetate, washed with water and dried over sodium sulfate and the solvent is distilled off. 10 ml of methyl tert-butyl ether are added to the residue and the precipitate formed is filtered off with suction. After drying, 2.4 g of a white powder remain.

Workup

  1. stirringAfter stirring
  2. waithas been carried out for 24 hours at room temperature
  3. customhydrolysis
  4. distillationthe solvent is distilled off under greatly reduced pressure
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. distillationthe solvent is distilled off
  8. addition10 ml of methyl tert-butyl ether are added to the residue
  9. customthe precipitate formed
  10. filtrationis filtered off with suction
  11. customAfter drying

Sources & evidence

ORD record
ord-4382aaa227ba431685e9d8b00299cbfd
Source dataset
uspto-grants-1997_12
Patent number
US05703017

Reaction notes

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